I'm seeing the exact same thing. On a fresh Ubuntu Server 14.04.1
install:

root@server1:~# md5sum /sbin/start-stop-daemon
b1b8894ae2e3b547dca0e288634cce4a  /sbin/start-stop-daemon
root@server1:~# apt-get install --reinstall dpkg
Reading package lists... Done
Building dependency tree       
Reading state information... Done
0 to upgrade, 0 to newly install, 1 reinstalled, 0 to remove and 0 not to 
upgrade.
Need to get 1,954 kB of archives.
After this operation, 0 B of additional disk space will be used.
Get:1 http://gb.archive.ubuntu.com/ubuntu/ trusty-updates/main dpkg amd64 
1.17.5ubuntu5.3 [1,954 kB]
Fetched 1,954 kB in 0s (6,556 kB/s)
(Reading database ... 71661 files and directories currently installed.)
Preparing to unpack .../dpkg_1.17.5ubuntu5.3_amd64.deb ...
Unpacking dpkg (1.17.5ubuntu5.3) over (1.17.5ubuntu5.3) ...
Processing triggers for man-db (2.6.7.1-1) ...
Setting up dpkg (1.17.5ubuntu5.3) ...
root@server1:~# md5sum /sbin/start-stop-daemon
6a1ece8cbbe7d816dcdd83e79e837605  /sbin/start-stop-daemon

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https://bugs.launchpad.net/bugs/1363519

Title:
  start-stop-daemon fails debsums check

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